It was Wednesday afternoon, less than two weeks after I started the Best Job I Will Ever Have, when I realized this alarming fact:

I might have to sleep with my boss.

I don’t know why I hadn’t seen it before. The evidence was really stacked up against me. Every year my boss got a new assistant. Every year it was another young, single man. Every day she would take me out for a lunch that included at least a couple of drinks. And, if I was being honest with myself, I had to admit that I had absolutely no qualifications for this job, whatsoever.

That was the summer I worked at the Toronto International Film Festival. As festivals go, it’s not as glamorous as the one in Cannes or as “important” as the one in Park City, but it’s bigger than both of them. And, because it happens in the early fall, the Hollywood studios use it as a place to launch their potential Oscar-winners. Which means a ton of studio execs, cigar-chomping producers and Hollywood Movie Stars crash into town for the week. Which, in turn, means that nobody really bothers to attend the movie screenings, because they are too busy trying to score tickets to the invite-only, VIP parties.

My boss was the Queen of those Festival Parties. Officially, she was the Special Events Director for the festival. Unofficially, she was the keeper of the keys to the magic kingdom – the one person who could get you into any exclusive event for the chance to rub shoulders with Martin Scorsese and Al Pacino or Clooney and Brad and Angelina. Her name was Party Barbara. She definitely lived up to the moniker. Years of late nights and countless packs of du Maurier Lights had given her voice this distinctive rasp that was two parts Kathleen Turner, one part Tom Waits.

I was Party Barbara’s Boy Friday. Unfortunately for her, I had no experience, or aptitude, for party planning. Like most people in the movie business, I got the job because I knew someone. Barbara was friends with my old boss at MGM, who had recommended me for the job, well, honestly, because I was working at MGM for free and they didn’t have enough work or budget to give me a paying job. And Tammy, bless her heart, wanted me to have the chance to put a couple of dollars in my pocket over the summer and get a taste of what it’s like on the other side of the velvet rope. My job, from what I could tell, was to do whatever Barbara told me. Mostly I answered the phone, set up meetings, made deliveries and drank whatever fancy cocktails she ordered for me. It was also entirely possible that my duties could expand to include seeing my boss naked before the end of the summer. The good news was that, as a recent college grad, my alcohol tolerance was quite high. The bad news was that, as a recent college grad, my moral standards were quite low.

My contract was ten weeks long. Eight weeks of party planning and prep and then two weeks of non-stop festival events and late-night parties. This gave me about eight and a half weeks to keep my conscience clear and my innocence intact. Clearly, I needed a plan.

I turned to a good friend from college for help. Jamie was a clever young fellow. The proud owner of a Masters degree in something or other and now enrolled in law school. I offered to trade pints for advice and by our sixth beer at the Imperial, he’d clearly laid out my three options for me:

I could quit. Hand in my walking papers and never see Party Barb again. The simplest and cleanest of all my choices, except for the fact that I’d be out of a job and a paycheck. This wasn’t really an option, since I’d just spent the last 6 months working in the MGM mailroom for $0.00/hour and all the pens I could steal.

I could pretend I was gay. This would have been a possibility except that (a) I’m a terrible actor, and (b) I’d already been hit on by the 60-year-old programmer of the Festival’s gay and lesbian film series and had told him in no uncertain terms that I was not on “his team” while Barbara sat right beside me. Which is a shame, really, because if I’d pulled this one off I could have gone on to turn the story of my hijinks into a totally wacky sitcom starring Neil Patrick Harris.

I could grow a spine. No means no, after all. I could do my job like anyone else and put my foot down if she pressed the issue.

Photo by Alexa Clark

In the cold, green light of that neon sign hanging behind the bar, Jamie’s logic was undeniable. With a belly full of liquid courage, option three was looking pretty good, but I hadn’t entirely ruled out option two. I bought the next round, secure in the knowledge that tomorrow morning, the right answer would become clear.

The next thing I remember, it was 8:45 am on Thursday morning. Oh, shit. This was bad. I dove in and out of the shower, jumped on my bike and pedaled furiously down College Street.1 But all that training for my failed career as a bike messenger wasn’t going to do me a bit of good now. I was going to be late and Barbara was going to be pissed. And you don’t want to see Barbara when she’s angry.

I stopped at Starbucks on my way to the elevator and lurched into the office, holding Barbara’s coffee out in front of me like a Grande Non-Fat Caramel Macchiato shield.

“Sorry I’m late – I brought Starbucks!” I braced for impact.

But the office was empty. Thank god. I put Barbara’s coffee on her desk, sat down and checked my messages. Ninety minutes later, I’d finished both coffees and sent two dozen emails, but still no word from the boss lady. I was beginning to worry. That’s when the phone rang.

“Good morning, Party Barbara’s office.” I chirped as best as I could.

“Tony…” rasped a voice from deep, down in the basement.

Confused, I said nothing. How did James Earl Jones get this number? And how did he know my name? The voice from the deep cleared its throat loudly and spoke again, with more urgency.

“Tony! It’s me.”

Wait – I knew that voice. It wasn’t the Dark Lord of the Sith. It was my boss, only she’d modified the recipe for her voice, adding one part Lindsay Lohan and two parts Darth Vader.

“Barbara? Is that you? Are you OK?”

“God, I’m hung-over,” she growled. “I’m still in bed. What time is it?”

“It’s almost 11:00.”

“Oh fuck. If anyone asks – I had a meeting with the caterer this morning. I’ll be there soon.”

When she arrived a few hours later, we took a long lunch and I confessed that I was also hung-over and late for work today. This was the first real bonding moment for Barbara and I. Maybe I didn’t know the first thing about party planning, but at least I knew how to get drunk on a school night and still make it to the office the next morning. Which, as I would soon find out, was one of the few true requirements for an employee of the party department. We split a travel package of Advil and she gave us both the rest of the day off.

Fast-forward to the end of the summer and the festival was almost upon us. Two months of planning and organizing and arranging had raced by and my innocence was still intact. Perhaps improved performance in some areas of my work meant that I wouldn’t be required to perform in other ways? I’m feeling cautiously optimistic.

I’m also distracted by the flood of A-Listers jetting into town. The building is abuzz with gossip about star sightings and encounters. I bump into Parker Posey in the lobby. Michelle in the publicity office swears she saw Demi Moore’s car parked outside of the Betsey Johnson boutique in Yorkville. Demi wanted to shop, but she didn’t want to actually go into the store. So, she sat in the air-conditioned comfort of her black stretch limo while her assistant ran in and out of the store, grabbing outfit after outfit and responding to Demi’s demands.

“Do they have that in orange?”

“Find me a belt to go with that one.”

“Can you try it on for me?”

Apparently, if you want to be Demi Moore’s assistant, you need to be her size.

But enough about Demi. Let’s talk about the reason she had finally arrived and was furiously shopping for evening wear:

It was time for Opening Night.

on the red carpet

The party was embarrassingly extravagant. Barbara never really told me how much money the festival was dropping on the opening bash, but I’ll bet if you had that amount in cash, you’d need at least a dozen bathtubs to hold it. We rented a huge, empty department store and decorated it from the ground up. Six thousand guests. Three floors. Each with a different theme and color scheme. Each with its own bar and food and entertainment. A 12-piece jazz band played in the lounge on the top floor, next to a row of tables where well-dressed gentlemen hand-rolled Cuban cigars. Half of the second floor was converted into a nightclub, complete with a spinning disco ball and a dance floor that lit up like Tony Manero’s own in Saturday Night Fever. An epic red carpet extended out to the street to welcome the fabulous and glamorous2 as they arrived.

The booze flowed endlessly and the party stretched on late into the night and then spilled over into the Bistro 990 – a fancy-pants French restaurant that had a special license to serve until 4:00 in the morning. Just before the wheels came off, I managed to pour myself into a cab and get home for a few hours of sleep.

The next day we moved our office into the Sutton Place Hotel, where we’d stay for the remainder of the festival. And, because my boss was the High Priestess of Sweet Hookups, I found myself working out of a luxurious suite on the 22nd floor. Barbara also had a direct line to the concierge desk and room service and she wasn’t afraid to use it.

That first afternoon in the hotel, at the time when normal people with normal jobs would take a coffee break, Party Barbara looked over at me and shouted in her raspy rasp, “I feel like a Caesar.3 Let’s get a round of Caesars.”

And suddenly we were drinking cocktails in a fancy hotel suite in the middle of the afternoon. When she ordered the second round, I began to get nervous.

“Hey,” Barbara barked, “You want a shot?”

At this point, I should mention that there was a King-sized bed just on the other side of the door next to my desk.

Before I could answer, a doctor burst into our room and pulled out a packet of syringes and a pair of latex gloves. Barbara got up from her chair and started to unfasten her belt. I began to perspire. Clearly, this was the moment of truth. One of those times in a young man’s life when he is forced to test his mettle and see what he’s made of.

I ran for it. Seriously – I mumbled some excuse about needing to use the restroom and bolted out the door. At first I wasn’t even sure where I was headed, but I quickly realized there was only one person who could help me in this moment: Michael, Barbara’s old assistant. He worked in the fund-raising and development office now, but he’d been in my shoes before. I raced into his office.

“Michael can I ask you something?” I was sweaty, panicked and a little bit drunk, but I had nowhere else to turn. “Do I have to sleep with her?”

“Do you have to sleep with who?” Michael seemed remarkably calm, if a little confused.

“Barbara! Do I have to sleep with Barbara? I know she always hires young guys for assistants. Is this part of the job? Did you have to sleep with her?”

Michael giggled. “Tony, I’m gay.”

“But I’m not!” I shrieked.

“OK, settle down Ashton Kutcher. Barbara doesn’t hire young boy toys so she can fuck them. She just prefers to work with men. And, between you and me, I think she enjoys bossing young men around.”

It turns out that the syringes weren’t for anything kinky, either. They were just vitamin B-12 shots. I headed back to our office to finish my Caesar and get a needle stuck in my ass. As I said before – best job ever.

With the pressure off and the festival in full swing, the party department quickly fell into a rhythm. Stay at the office until 4:00 in the pm. Head home for a nap. Out to dinner and the first of many events, and then on to whatever after-party party was happening, and finally back to the Bistro 990 for a nightcap. Show up at the office by 10:00 the next morning and repeat. Needless to say, the week went by in a blur. Before I knew it, Closing Night was upon us.

The Festival’s Closing Night film was Tom Hanks’ directorial debut – a fun little movie about 60’s pop music called That Thing You Do. Barbara was a big Tom Hanks fan and she really wanted the party to be a hit. We even watched the movie together to get ideas for party themes. It was a huge indoor / outdoor affair complete with live bands, a state fair-style midway packed with carnival games and an exclusive VIP area up above that literally looked down on the rest of the party. As this was the last night of the festival and I didn’t have to be at work the next day, I snuck in a few of my friends to share in the fun and free food and booze.

By midnight, everyone was having a really excellent time, but my friend Dr. Steve had decided that we needed to do something extra special to make this a real night to remember.

We needed to meet Liv Tyler.

photo by FlynetPictures.com

A swell idea, for sure, but how to get close to her? Barbara could get me into the VIP area, but since Dr. Steve wasn’t even supposed to be at the party, it was off-limits for him. Still, we would not to be denied. If there’s one thing I learned from Party Barbara, it’s that if you know the right people, you can always get what you need. In this case, I knew the security guys.

You see, the thing about throwing a party with an open bar for 6,000 of your closest friends is that eventually, inevitably, long lines form at the restrooms. In particular, at the ladies room. At this late hour, there must have been fifty or more women lined up at every restroom in the building. And from our pre-party prep, I knew that while we had a VIP area, this particular facility did not come equipped with VIP restrooms. Of course, you can’t invite Liv Tyler to a party and then ask her to wait in line to pee. So, our security team had developed a unique little system.

Whenever Liv needed the ladies, she’d tell Roland, the head of security. Two of Roland’s guys would escort Ms. Tyler right into one of the men’s restrooms, stand in front of her stall while she took care of business, and then escort her out again.

For our plan to come together, all I had to do was ask security to give me a heads up the next time Liv took a potty break.

When we got the good word from Roland, Dr. Steve and I hustled over to the men’s room in question. We made note of the stall being guarded by two burly gentlemen and then proceeded to wash our hands for a very, very long time.

And then it happened. Dr. Steve looked up and found himself sharing a men’s room mirror with one of the most beautiful women in the world.4 Now, some men will find themselves in these types of situations and freeze up, but Dr. Steve had been planning this all night (all his life, really) and he wasn’t going to let the moment pass. He opened with his best material:

“Hi.”

Liv smiled back at him. “Hi.”

I jumped in as we all reached for the hand towels, “I really liked the movie.”

She was gracious in her reply, “Thanks.”

We all walked for the door together. Liv got the final word:

“Nice to meet you.”

And then she was gone. Dr. Steve went for a high five. I would not see a bigger smile on this man’s face until I attended his wedding nearly a decade later. He raced off to call our friends at home and brag about the epic moment we had just experienced.

On that note, I decided it was time to wrap up the final party of the final day of the Best Job I Will Ever Have. I said goodbye to my boss lady, stopped by the bar for one last complimentary cocktail and headed home to spend the rest of the weekend sleeping it off.

As it turns out, that would be the last time I ever saw Party Barbara. But just like Liv Tyler, she managed to get in the last word. A week later, two cases of wine arrived at my front door along with a hand-written note:

“Party on! Love, PB.”

You know I will, Party Barbara. You know I will.

No, I didn’t have a car. Did you miss the part about how I’d been working for free for six months? [↩]

I even managed a few star sightings of my own. And because I know everyone loves a little Hollywood gossip, here is a quick summary of what I learned behind that velvet rope: Al Pacino is very short. Angelica Houston is very tall. Charlize Theron is even taller. Jennifer Tilly is not putting on that voice. And, Tom Hanks is just as genuinely nice in person as he appears on screen. Later in the week, I would even meet Liv Tyler under very unusual circumstances, but I’ll get back to that later. [↩]

The Caesar (or Bloody Caesar) is a uniquely Canadian cocktail. Imagine a Bloody Mary with a dash of clam juice and a stalk of celery for a stir stick. I know it sounds awful but trust me, that shit is delicious. [↩]

This entry was posted on Monday, March 12th, 2012 at 8:58 pm and is filed under stories. You can follow any responses to this entry through the RSS 2.0 feed.
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